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Synthesis, Characterization of Two Chiral Tertiary Ferrocenylamines and Their Cyclopalladations

Author: YangXiaoLi
Tutor: WangHongXing
School: Tianjin University
Course: Organic Chemistry
Keywords: Acetylferrocene Benzylamine Central palladium reaction Stereoselective
CLC: O621.25
Type: Master's thesis
Year: 2007
Downloads: 40
Quote: 0
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Abstract


In anhydrous ethyl ether, acetyl ferrocene with (R) and (S)-α-methylbenzyl amine condensation catalyzed by titanium tetrachloride were obtained Schiff alkali (RC) - [(η 5 -C 5 H 5 ) Fe (η 5 -C 5 H 4 CCH 3 = NCHCH 3 C 6 H 5 )] and (SC) - [ (η 5 -C 5 H 5 ) Fe (η 5 -C 5 H 4 CCH 3 = NCHCH 3 C 6 H 5 )]. Methanol / sodium borohydride reduction to give the secondary amine compound (RC6, RC8) - [(η 5 -C 5 H 5 ) Fe (η 5 -C 5 H 4 CHCH 3 NHCHCH 3 C 6 H 5 )] and (SC6, SC8) - [(η 5 -C 5 H < sub> 5 ) Fe (η 5 -C 5 H 4 CHCH 3 NHCHCH 3 C 6 H 5 )]. Secondary amine compound as a solvent, sodium cyanoborohydride in acetonitrile / 37% formaldehyde solution reductive methylation to give a tertiary amine (RC6 is RC8) - [(η 5 -C < sub> 5 H 5 ) Fe (η 5 -C 5 H 4 CHCH 3 NCH 3 CHCH 3 C 6 H 5 )] and (SC6, SC8) - [(η 5 -C 5 H5) Fe (η 5 -C 5 H 4 CHCH 3 NCH 3 CHCH 3 C 6 H 5 ) ]. A tertiary amine compound in methanol / dichloromethane as the solvent, sodium tetrachloropalladate ring palladium reaction for the case of palladium reagents, to give the ring a palladium compound {(RC6, SN, RC8, RP)-σ-Pd [(η 5 -C 5 H 5 ) Fe (η 5 -C 5 H 3 CHCH 3 NCH 3 CHCH 3 C 6 H 5 < / sub>)] Cl (PPh 3 )} and {(SC6 is, the RN, SC8)-σ-Pd [(η 5 -C 5 H 5 ) Fe (η 5 -C 5 H4CHCH 3 NCH 3 CHCH 3 C 6 H 4 )] Cl (PPh 3 )}. More than secondary amines, tertiary amines, as well as ring palladium compounds were confirmed by elemental analysis, IR, NMR. In addition, two ring palladium product has also been confirmed by X-ray ring palladium reaction regioselectivity and stereoselectivity discussed.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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